Benzylfentanyl

Benzylfentanyl (R-4129) is a fentanyl analog.[1] It was temporarily placed in the US Schedule I by emergency scheduling in 1985 due to concerns about its potential for abuse as a designer drug, but this placement was allowed to expire and benzylfentanyl was formally removed from controlled substance listing in 2010, after the DEA's testing determined it to be "essentially inactive" as an opioid.[2] Benzylfentanyl has a K_i of 213 nM at the mu opioid receptor, binding around 1/200 as strong as fentanyl itself,[3] though it is still slightly more potent than codeine.[4]

Benzylfentanyl

Names
IUPAC name N-(1-Benzylpiperidin-4-yl)-N-phenylpropanamide
Identifiers
CAS Number	1474-02-8
3D model (JSmol)	Interactive image
ChemSpider	220920
ECHA InfoCard	100.014.559
PubChem CID	252141
UNII	9BV2D1A57H
CompTox Dashboard (EPA)	DTXSID00163705
InChI InChI=1S/C21H26N2O/c1-2-21(24)23(19-11-7-4-8-12-19)20-13-15-22(16-14-20)17-18-9-5-3-6-10-18/h3-12,20H,2,13-17H2,1H3 Key: POQDXIFVWVZVML-UHFFFAOYSA-N
SMILES CCC(=O)N(C1CCN(CC1)CC2=CC=CC=C2)C3=CC=CC=C3
Properties
Chemical formula	C21H26N2O
Molar mass	322.452 g·mol^−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Side effects of fentanyl analogs are similar to those of fentanyl itself, which include itching, nausea, and potentially serious respiratory depression which can be life-threatening. Fentanyl analogs have killed hundreds of people throughout Europe and the former Soviet republics since the most recent resurgence in use began in Estonia in the early 2000s, and novel derivatives continue to appear.[5]

Legal status

In the United States, fentanyl-related substances are Schedule I controlled substances.[6] Benzylfentanyl is illegal in Germany (Anlage I)

See also

• Isofentanyl

References

1. Ruangyuttikarn, W; Law, MY; Rollins, DE; Moody, DE (1990). "Detection of fentanyl and its analogs by enzyme-linked immunosorbent assay". Journal of Analytical Toxicology. 14 (3): 160–4. doi:10.1093/jat/14.3.160. PMID 2374405.
2. Correction of Code of Federal Regulations: Removal of Temporary Listing of Benzylfentanyl and Thenylfentanyl as Controlled Substances
3. Utilization of a radioreceptor assay for the analysis of fentanyl analogs in urine Mario Enrique Alburges
4. Chen ZR, Irvine RJ, Somogyi AA, Bochner F (1991). "Mu receptor binding of some commonly used opioids and their metabolites". Life Sci. 48 (22): 2165–71. doi:10.1016/0024-3205(91)90150-a. PMID 1851921.
5. Jane Mounteney; Isabelle Giraudon; Gleb Denissov; Paul Griffiths (July 2015). "Fentanyls: Are we missing the signs? Highly potent and on the rise in Europe". The International Journal of Drug Policy. 26 (7): 626–631. doi:10.1016/j.drugpo.2015.04.003. PMID 25976511.
6. Drug Enforcement Administration, Department of Justice (2018). "Schedules of Controlled Substances:Temporary Placement of Fentanyl-Related Substances in Schedule I. Temporary amendment; temporary scheduling order". Federal Register. 83 (25): 5188–92. PMID 29932611.